We are moving for work, and I want to purchase a fixer upper in the new location that will eventually be another house hack, but it may be a few years before we would rent it out. 

Just set aside some for repairs and to replace worn out or damaged items.All houses will eventually need a new roof or HVAC system.We also have an upgrade budget.

I can and will eventually work again (I'm an architect and psychologist), but would first like to explore my options that would allow me to develop this investment full-time.

I was curious about who and what they were and eventually joined their RE division as a broker and worked with our wonderful team from 2020-2023.

Just a thought.Depends on if you have cash reserves to cover the pipe replacement now; if not, you could save a certain amount each month to put towards eventual replacement.I guess you just have to decide if you want to pay to have the pipes replaced now, or at an unexpected time in the future. 

This will help with your comps knowing that they will eventually be used in your appraisal.

As such your underwriting should treat this as a duplex.I suspect eventually virtually all of Chicago will allow additional units but it could quite a few years.  

Now after consulting with a number of RE CPAs I found out that the legal structure you created is the most tax inefficient strategy for california residents and eventually I may be paying a big tax bill year end unless I do a major surgery and spend a lot more money to get it fixed. let me know if we can 1:1 sometime soon to discuss it more

Will these folks prefer to buy suburban or rural homes, or will they want to rent and eventually buy within the city?

Eventually, once the units have appreciated a bit and the mortgage has been paid down to the point we have 20% equity, we split the parcels into individual town homes and then she refinances her unit out and I refinance the three units out or sell them.